CHAPTER 7 - Practice Exercises (ORGANIC CHEM I ) ________DR.

PAHLAVAN
1. Write a complete reaction for the followings. Please show the stereochemistry of the product and explain why
a mixture is formed (if any).
a) Dehydration of 3-methyl-3-hexanol in aqueous sulfuric acid
) !reatment of "-romo-"-methylutane with #$% in ethanol
c) !reatment of 1&"-dimethylcyclohexene with 'l"
d) (ddition of %'l to 1&"-dimethylcyclohexene
e) )eaction of cyclopentene with *+, and water in D-,$
". Predict the products of the reactions of followings compounds with gi.en reagents. Please indicate
regiochemistry when rele.ant.

/)
//) ///)
a) %
"
0Pt ) +r
"
c) %+r d) $s$
1
0*a%,$
3
e) 'l
"
0%
"
$ f) #-n$
1
0%
3
$
g) %g(o(c)
"
& %
"
$ 0 *a+%
1
h) $
3
0 2n& %
3
$ i) +%
3
&!%3 0 %
"
$
"
& $%
4) '%'l
3
0 #$%
5) '%
"
/
"
0 2n('u) l) 'l
"
0 '%
"
'l
"

3. Descrie how to distinguish etween the memers of the following pairs of compounds y a simple chemical
test. 3or the pair& tell what test to perform& what you expect to oser.e& and write an equation for each
positi.e test. 3or example& to distinguish etween cyclohexane and 1-hexene& you might consider the reaction
of each with +r" in ''l1 or reaction with #-n$1 in asic solution.
a) cyclohexane and 1-hexene ) 1-hexene and "-chlorohexane
1. %ow would you carry out the following transformations6 /ndicate the reagents you would use in each case6

e)
a)
6
$%
$%
)
6
c)
6
'
'l
'l
6
%
$
d)
'%
3
$%
6
'%
3
$
1
7. ,uggest structures for al5enes that gi.e the following reaction products. !here may e more than one answer
for same cases.

a)
6
%
"
0 Pt& '
'%
3
'%
3
)
6
%'l
'l
'%
3
c)
6
%g ($(c)
"
& %
"
$
*a+%
1
1)
")
$%
d) 6
+r
"
+r
+r
e) 6
$
3
0 2n & %
3
$
% - ' - '%
"
- '%
"
- '%
"
- '%
"
- ' - '%
3
$ $
8. )oad map prolem- What are the structures of compounds (& +& '& and D6

'ompound ( ('
9
%
9
)
#-n$
1
'$
"
: 'aroxylic acid
+ ( '
;
%
8
$
"
)
1 %
"
reduce aromatic
ring
'
9
%
18
(')
1 molar
equi.alent %
"
0Pd
'ompound (D)
;. ( compound has a formula '1<%18. $n catalytic hydrogenation o.er palladium& it reacts with only 1 mole
equi.alent of %". 'ompound ( also undergoes reaction with o=one& followed y =inc treatment& to yield a
symmetrical di5etone + ('1<%18$"). /dentify the structures for compounds ( and +.
"
9. ,how how to con.ert cyclopentene into these compounds. Please show all the steps clearly.
a)
+r
+r
)
$%
$%
c)
$%
d)
+r
e)
/
f) g)
' - ('%
"
)
3
- '
$ $
%
%
>. Propose a mechanism& using cur.ed arrows to show electron mo.ement for each step.
a) hydroromination of 1-methylcyclohexene
) acid cataly=ed addition of "-methylpropene with '%3$% in presence of %",$1
c) romination of 1-methylcyclohexene
d) oxymercuration hydration of 1-methylcyclohexene in sodium orohydride
e) romohydration of "-methypropene
1<. ,how y a series of reactions how could you prepare the following compounds from the indicated starting
compound. +e sure to clearly indicate the reagents used in each step.


a)
$%
'l
d)
'%
3
-'%
"
- '%
"
- '%
"
+r '%
3
-'%
"
- '%+r - '%
3
) ' - ('%
"
)
1
- '
% %
$
$
c)
'%
3
+r
'%
3
+r
$%
3
11. Draw structural formulas for the products of the following reactions. Predict which is the ma4or product.


a) '%
3
- ' ? '% - '%
3
'%
3
%
"
$ 0 %
"
,$
1
)
+r
"
0 ''l
1
c)
'%
3
1) +%
3
& !%3
") %
"
$
"
& $%
d)
*+, 0 light
e)
*+,
%
"
$ & D-,$
(halohaydration)
( allylic romination)
f) '%
3
- ' ? '% - '%
"
- '%
3
'%
3
1) $
3
") 2n& %
3
$
g)
'%
3
- '% - '% - '%
3
'%
3
+r
heat
h)
+r
"
0%
"
$
i)
1) %g($(c)
"
& %
"
$
") *a+%
1
4)
#-n$
1
#$%

1